Hydrochloric Acid → N-(5-amino-2-chloropyridin-3-yl)morpholine-4-sulfonamide

HRID 1812360

Reaktionsgleichung

Reaktionsgleichung von HRID 1812360
[Cl:1][C:2]1[C:7]([NH:8][S:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:6][C:5]([N:18]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][N:3]=1.Cl>C1COCC1>[NH2:18][C:5]1[CH:6]=[C:7]([NH:8][S:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[C:2]([Cl:1])=[N:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86647078N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-sulfonamide

Produkt 1

HCID 71481004N-(5-amino-2-chloropyridin-3-yl)morpholine-4-sulfonamideAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The two batches of N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-sulfonamide (total 0.47 g, 1.0 mmol) were placed in two 150 mL round-bottomed flasks. To each flask were added 1 N hydrochloric acid (0.6 mL each, total 1.2 mL) and 3 mL THF (3 mL each, total 6 mL). After stirring at room temperature for 10 min, the two reaction mixtures were combined and most of THF was removed in vacuo, and the residue was partitioned between saturated aqueous ammonium chloride (30 mL) and 25% isopropanol in chloroform (30 mL). The aqueous phase was extracted with 25% isopropanol in chloroform (2×20 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (25 g, eluent: iPrOH in CHCl3 0% to 10%) to afford N-(5-amino-2-chloropyridin-3-yl)morpholine-4-sulfonamide (0.233 g, 77% yield) as a light brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.64 (d, J=2.74 Hz, 1H) 7.30 (d, J=2.74 Hz, 1H) 6.68 (br. s., 1H) 3.83 (br. s., 2H) 3.66-3.71 (m, 4H) 3.22-3.27 (m, 4H). m/z (ESI, positive ion): 293.0 (M+H)+.

Aufarbeitung

  1. customthe two reaction mixtures
  2. customwas removed in vacuo
  3. customthe residue was partitioned between saturated aqueous ammonium chloride (30 mL) and 25% isopropanol in chloroform (30 mL)
  4. extractionThe aqueous phase was extracted with 25% isopropanol in chloroform (2×20 mL)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography (25 g, eluent: iPrOH in CHCl3 0% to 10%)

Quellen und Nachweise

ORD-Eintrag
ord-f175e30932634e3d84351e1c31f2875f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362241B2

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